28343-22-8Relevant articles and documents
Isolation and identification of a potent radical scavenger (canolol) from roasted high erucic mustard seed oil from nepal and its formation during roasting
Shrestha, Kshitij,Stevens, Christian V.,De Meulenaer, Bruno
, p. 7506 - 7512 (2012)
Roasting of high erucic mustard (HEM) seed has been reported to give a typical flavor and increase the oxidative stability of the extracted oil. A potent radical scavenging compound was successfully isolated from roasted HEM seed oil in a single-step chromatographic separation using an amino solid-phase extraction column. Nuclear magnetic resonance and mass spectrometry spectra revealed the compound as 2,6-dimethoxy-4-vinylphenol (generally known as canolol), and its identity was fully confirmed by chemical synthesis. The formation of canolol during roasting was compared among HEM varieties (Brassica juncea, B. juncea var. oriental, Brassica nigra, and Sinapis alba) together with a low erucic rapeseed variety. HEM varieties were shown to produce less than one-third of canolol compared to rapeseed at similar roasting conditions. This observation was linked to a lower free sinapic acid content together with a lower loss of sinapic acid derivatives in the HEM varieties compared to rapeseed. Around 50% of the canolol formed in the roasted seed was shown to be extracted in the oil. Roasting of HEM seed before oil extraction was found to be a beneficial step to obtain canolol-enriched oil, which could improve the oxidative stability.
Production of canolol from canola meal phenolics via hydrolysis and microwave-induced decarboxylation
Khattab, Rabie Y.,Eskin, Michael N.A.,Thiyam-Hollander, Usha
, p. 89 - 97 (2014)
A potent antioxidant, anti-inflammatory and anti-mutagenic agent; 4-vinyl-2,6-dimethoxyphenol (canolol) was obtained from canola meal in a significant yield via alkaline (NaOH)/enzymatic (ferulic acid esterase) hydrolysis followed by microwave-assisted decarboxylation. The hydrolysis was carried out either through using canola meal directly as a substrate or by using the 70 % aqueous methanolic extract filtrates. The hydrolyzed extracts underwent RP-HPLC analysis which showed that 81.0 and 94.8 % of the total phenolics were hydrolyzed to sinapic acid after the alkaline hydrolysis of the meal and the methanolic extracts, respectively. The enzymatic hydrolysis showed lower conversion rates (49.5 and 58.3 %). The hydrolyzed extracts were consequently decarboxylated using 8-diazabicyclo[5.4.0]undec-7-ene under microwave irradiation at different conditions. The HPLC profiling of decarboxylated extracts showed that using microwave at 300 Wof microwave power for 12 min brought the highest sinapic acid conversion to canolol (58.3 %) yielding 4.2 mg canolol from each gram of canola meal suggesting that the process could be commercially economical. AOCS 2013.
Antioxidant activity of soybean oil containing 4-vinylsyringol obtained from decarboxylated sinapic acid
Wang, Xiang-Yu,Yang, Dan,Jia, Cai-Hua,Shin, Jung-Ah,Hong, Soon Taek,Lee, Ki-Teak,Zhang, Hua,Lee, Yong-Hwa,Jang, Young-Seok
, p. 1543 - 1550,8 (2014)
4-Vinylsyringol was produced by decarboxylation from sinapic acid. To evaluate the antioxidant activity of 4-vinylsyringol, 500 ppm of 4-vinylsyringol, sinapic acid, or α-tocopherol was added to soybean oil and the oxidation processes were monitored by the peroxide value (PV), the thiobarbituric acid reactive substances value (TBARS) assay, and 1H-NMR spectroscopy. The results obtained by PV and TBARS indicated that soybean oil containing 4-vinylsyringol (SBO-VS) showed the highest oxidative stability. 1H-NMR analysis also showed concurring results. After 19 days of oxidation, the degradation rates of linoleic acid (4.2 %) and linolenic acid (4.4 %) in SBO-VS were significantly lower than those in other oils. Secondary oxidation products (i.e. aldehydes) were undetectable in SBO-VS by 1H NMR, whereas concentrations of such compounds in soybean oils containing α-tocopherol or sinapic acid were 38.0 ± 0.4 and 2.75 ± 0.2 mM oil, respectively. In addition, synergistic antioxidant effect between any two antioxidants was not observed.
New hybrids based on curcumin and resveratrol: Synthesis, cytotoxicity and antiproliferative activity against colorectal cancer cells
Cardona-G, Wilson,Hernández, Cristian,Herrera-R, Angie,Moreno, Gustavo
, (2021)
We synthesized twelve hybrids based on curcumin and resveratrol, and their structures were elucidated by spectroscopic analysis. The chemopreventive potential of these compounds was evaluated against SW480 human colon adenocarcinoma cells, its metastatic derivative SW620, along with the non-malignant CHO-K1 cell line. Among the tested compounds, hybrids 3e and 3i (for SW480) and 3a, 3e and 3k (for SW620) displayed the best cytotoxic activity with IC50 values ranging from 11.52 ± 2.78 to 29.33 ± 4.73 μM for both cell lines, with selectivity indices (SI) higher than 1, after 48 h of treatment. Selectivity indices were even higher than those reported for the reference drug, 5-fluorouracil (SI = 0.96), the starting compound resveratrol (SI = 0.45) and the equimolar mixture of curcumin plus resveratrol (SI = 0.77). The previous hybrids showed good antiproliferative activity.
Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins
Yang, Biao,Dong, Kui,Li, Xiang-Sheng,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 2040 - 2044 (2022/03/17)
An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.
Profiling of the formation of lignin-derived monomers and dimers from: Eucalyptus alkali lignin
Hu, Zhenhua,Li, Suxiang,Lu, Fachuang,Shi, Lanlan,Wang, Chen,Yue, Fengxia,Zhang, Han,Zhao, Chengke
supporting information, p. 7366 - 7375 (2020/11/18)
Lignin is a renewable and the most abundant aromatic source that can be used for extensive chemicals and materials. Although approximately 50 million tons of lignin are produced annually as a by-product of the pulp and paper industry, it is currently underutilized. It is important to know the structural features of technical lignin when considering its application. In this work, we have demonstrated the formation of low-molecular-weight constituents from hardwood (Eucalyptus) lignin, which produces much more low-molecular-weight constituents than softwood (spruce) lignin, after a chemical pulping process, and analyzed the micromolecular compositions in the alkali lignin after fractionation by dichloromethane (DCM) extraction. By applying analytical methods (gel-permeation chromatography, 2D NMR and GC-MS) with the aid of evidence from authenticated compounds, a great treasure trove of lignin-derived phenolic compounds from Eucalyptus alkali lignin were disclosed. Except for some common monomeric products, as many as 15 new lignin-derived monomers and dimers including syringaglycerol, diarylmethane, 1,2-diarylethanes, 1,2-diarylethenes, (arylvinyl ether)-linked arylglycerol dimers and isomeric syringaresinols were identified in the DCM-soluble fraction. Regarding the formation and evolution of the Cα-condensed β-aryl ether structure, a novel route that is potentially responsible for the high content of β-1 diarylethenes and diarylethanes in the lignin low-molecular-weight fraction, in addition to the β-1 (spirodienone) pathway, was proposed. This work not only provides novel insights into the chemical transformation of S-G lignin during the alkali pulping process, but also discovered lignin-derived phenolic monomers and dimers that can potentially be used as raw materials in the chemical or pharmaceutical industries. This journal is
